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Strategic Applications of Named Reactions in Organic Synthesis. Background and Detailed Mechanisms. By Laszlo Krti and Barbara Czako

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Angewandte
Books
Chemie
Modern Cyclophane Chemistry
Edited by Rolf
Gleiter and Henning
Hopf. Wiley-VCH,
Weinheim 2004.
566 pp., hardcover
E 149.00.—ISBN
3-527-30713-3
The present book, Modern Cyclophane
Chemistry, is best classified as an extensive monograph consisting of 20 chapters, written by a group of authors
whose names read like a “Whos
Who?” of cyclophane chemistry. The
book is clearly written for the academic
researcher/lecturer and graduate students in the field of organic chemistry.
On over 500 pages, it contains everything the reader always wanted to
know, but never dared to ask, about
cyclophane chemistry.
The book fits well into the vastly
popular “Modern …” series from
Wiley-VCH: Modern Acetylene Chemistry I and II, Modern Arene Chemistry,
Modern Allene Chemistry, etc., and has
the same aspiration to quality and comprehensiveness. Overall, it is a superb
book, edited by two giants in the field
of cyclophane chemistry.
I have read a few of the 20 chapters
and has browsed through the rest of
them. The first impression is that of a
very carefully edited and asthetically
pleasing opus. All of the chapters are
well structured, pedagogically valuable,
and easily readable, and give excellent
references to published material, including work of the authors and of other
groups. The use of graphics, figures,
Angew. Chem. Int. Ed. 2005, 44, 5005 – 5006
and pictures is very appropriate and
helps in the easy understanding of the
topics that are discussed. A significant
amount of information could be gleaned
from the beautiful, carefully done, and
high-quality graphics. This monograph
gives an excellent historical overview,
as well as a timely review of the evergrowing and fascinating field of cyclophane chemistry. A particularly attractive feature for academic teachers is
the inclusion of many exciting structures
and reactions, which can easily be used
for topics in a graduate class. The book
describes sophisticated, yet important,
examples of organic reactions that are
valuable for the construction of non-natural products.
The subject index is easy to use, and
gives excellent access to the topics
treated in this volume. Particularly
advantageous is that the UV/Vis spectra
(Chapter 11) are tabulated and easily
accessible, almost as in a reference
book. Overall, it was a pleasant experience to read and review this excellent,
exciting, yet rounded monograph about
cyclophane chemistry, which should be
bought by interested graduate students
and university teachers. The book
should be in every library. Both the editors, as well as the authors of the individual chapters, did an excellent job in the
creation of this opus.
Uwe H. Bunz
School of Chemistry and Biochemistry
Georgia Institute of Technology
Atlanta, Georgia (USA)
Strategic Applications of Named
Reactions in Organic Synthesis
Background and
Detailed Mechanisms. By Laszlo
Krti and Barbara
Czako. Elsevier,
Amsterdam 2005.
757 pp., softcover
$ 94.95.—ISBN
0-12-429785-4
For the organic chemist engaged in synthesis, named reactions form a useful
and very special vocabulary, as the
name immediately conveys information
about the type of reaction, the starting
materials, the conditions required, and
the mechanism. In such a complex field
as organic synthesis, a vocabulary with
so concentrated an information content
serves as an efficient means of communication between chemists, and therefore named reactions occur very frequently in the chemical literature.
Two PhD students at the University
of Pennsylvania have written an impressive monograph that deals with the use
of classical and modern named reactions
as key steps in building up complex
organic molecules. This work sets new
standards, both in its comprehensiveness
and in the topicality of the examples discussed. The users who are likely to benefit from this rich source of information
range from the student who is seeking
details about a particular named reaction, to the university teacher who
wants quick access to up-to-date examples of certain transformations used in
the total synthesis of natural products.
The work begins with about 50 pages
that list common abbreviations, with
explanations and descriptions in the
form of text and structural formulas.
The authors describe 250 named reactions and named reagents, as well as
other transformations that are not
linked to a chemists name, such as
olefin metathesis. The selection covers
all the most important named reactions,
considered from the standpoint of their
use in complex organic syntheses. Each
named reaction is treated concisely on
two pages. In choosing the most appropriate names for the reactions, the
authors have followed a strict chronological principle, and it is pleasing to
see that their choices have overridden
any possible national or cultural prejudices.
The literature references are divided
into three groups: original publications;
review articles; variants and improvements. As there are, on average, about
40 references for each named reaction,
they have been collected together near
the end of the book. The authors have
searched the literature and compiled
the references with great care.
For each reaction, the first half-page
is occupied by a paragraph explaining its
importance. Related transformations
7 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5005
Books
are also mentioned, as well as significant
improvements in recent years. That is
followed by a general reaction scheme,
in which the individual components are
identified by colors. This color-coding
enables the reader to identify the different fragments that are mentioned in the
discussion that follows. The color system
is used consistently throughout the
book, and helps enormously in understanding the discussions. In addition to
a general reaction equation, other
related transformations are also shown,
with clear labeling where appropriate.
This lucid way of presenting the chemical relationships makes it easy for even
the less adept reader to understand.
The remaining part of this first page
shows mechanistic details, supported
by a concise paragraph of explanation.
The second page gives information
about the synthetic value and capabilities of the named reaction. The authors
describe three or four highly topical
5006
www.angewandte.org
and impressive examples of syntheses
in which the named reaction provides
the key step; in most cases the piece of
molecular framework that is synthesized
serves as a part of a larger complex natural product synthesis. Here again, by
skillfully combining text passages with
graphics showing other reactions leading to the target molecule, the authors
manage to build a remarkably coherent
picture.
Considering the size of the work, the
number of errors in the text and
schemes is on an acceptable level. However, despite the authors careful work,
the reader will come across some small
mistakes. For example, oxidation states
are sometimes given incorrectly
(p. 222), and on page 323 the target molecule, ( )-cryptopleurin, is shown
wrongly with an extra double bond. In
some cases, the mechanism indicated
does not reflect the latest knowledge:
for example, the Corey–Fuchs synthesis
7 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
of alkynes (p. 104) is now believed to
proceed via a carbenoid intermediate,
in analogy to the Fritsch–Buttenberg–
Wiechell rearrangement. Unfortunately,
the subject index fails to give many
important cross-references, and searching for a specific topic can be rather tedious.
However, no other book covers the
subject of named reactions in such an
up-to-date and comprehensive way,
ranging from mechanisms to applications. Despite its minor weaknesses, I
recommend this book most emphatically to interested chemists as a work
of reference and source of inspiration.
Siegfried R. Waldvogel
Kekul:-Institut f;r Organische Chemie
und Biochemie
Universit=t Bonn (Germany)
DOI: 10.1002/anie.200585304
Angew. Chem. Int. Ed. 2005, 44, 5005 – 5006
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